Total synthesis of (+)-4-deoxygigantecin

被引：25

作者：

Makabe, H

Tanaka, A

Oritani, T

机构：

[1] Tohoku Univ, Grad Sch Agr, Div Environm Bioremediat, Aoba Ku, Sendai, Miyagi 9818555, Japan

[2] Tohoku Univ, Fac Agr, Dept Appl Biol Chem, Aoba Ku, Sendai, Miyagi 9818555, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(98)00285-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis-tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from(S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+) -4-deoxygigantecin (1) by two steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6329 / 6340

页数：12

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